The judge declared a mistrial Tuesday, saying the jurors were "hopelessly deadlocked" after five days of deliberations in the San Diego County Superior Court.
A new trial date could be set by Friday, San Diego County prosecutor Dan Owens said.
Police allege he raped two women and exposed himself to a third woman last year; raped an unconscious teenager in 2003; and committed lewd acts in front of an elderly woman in February, according to court documents.
He was also acquitted of a second lewd conduct charge on Monday, according to a video of the courtroom proceedings.
CNN has reached out to Winslow's attorney for comment.
Owens said the "majority of jurors voted in favor of guilty" for the eight deadlocked charges but couldn't agree to a unanimous decision as required by California law.
The charges against Winslow spanned 16 years, from 2003 until February, and involved five women, according to court documents.
Winslow also faced misdemeanor charges of indecent exposure, willful cruelty to an elderly person, battery against an elderly person and two counts of lewd conduct.
Jurors remained deadlocked on several charges steaming from allegations that Winslow, 19 at the time and destined for the University of Miami, raped an unconscious 17-year-old, according to court documents.
The jury also deliberated over charges linked to incidents in 2018, involving a 54-year-old and a 59-year-old women, as well as cruelty and battery charges against a 77-year-old woman, according to prosecutors.
A judge revoked his bail in March after police accused him of lewd conduct involving a 77-year-old, jail records show. He was charged with lewd conduct for a February 13 incident and again for a February 22 incident involving the same woman. In the latter, Winslow was also charged with battery to and cruelty against an elderly person.
Winslow was selected No. 6 in the 2004 NFL draft. He spent four years with the Cleveland Browns before playing for the Tampa Bay Buccaneers, New England Patriots and New York Jets.
He is the son of former San Diego Chargers tight end Kellen Winslow.
CNN's Darran Simon and Sarah Moon contributed to this report.